Name: Islander Resort
Price range: £267
Rating: 9.4

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL

£199

7 Jul - 8 Jul

includes taxes & fees

Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...

9.2/10 Wonderful! (1,724 reviews)

"My girlfriend and I really enjoyed our time at Chesapeake. The room was immaculate and the view from our balcony was amazing. The staff was extremely friendly and helpful. I was able to use fishing gear from the front office to fish the beachfront and harbor in the evenings and they have kayaks available ..."

Reviewed on 17 Jun 2026

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL

£233

16 Jul - 17 Jul

includes taxes & fees

Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...

9.2/10 Wonderful! (1,317 reviews)

"We had a wonderful stay and really loved the resort. The room and balcony were absolutely perfect. My one suggestion would be to consider making one of the two beachfront pools adults-only. There is already an adults-only pool on the property, which is a nice option, but it’s located in the middle ..."

Reviewed on 15 Jun 2026

Islander Resort

82100 Overseas Highway Islamorada FL

£267

7 Jul - 8 Jul

includes taxes & fees

Stay at this beach hotel in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...

9.4/10 Exceptional! (1,050 reviews)

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Reviewed on 18 Jun 2026

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Breezy Palms Resort

80015 Overseas Highway Islamorada FL

Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...

8.8/10 Excellent! (698 reviews)

"First thing I noticed was how spotless the room was! I was impressed! Kudos to the cleaning staff. The kitchen was very well equipped with everything we could possibly need and the entire staff were super friendly and helpful! The pool is huge and there are plenty of seating choices both shaded and ..."

Reviewed on 17 Jun 2026

The Islands of Islamorada

82779 Old Hwy Islamorada FL

Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Florida Keys Brewing ...

9.6/10 Exceptional! (76 reviews)

"I am not usually about leaving reviews however this property definitely needs it. Heard a lot about being pampered when I was checked in and that they will bring you anything and to let them know what our needs were. Property does not have any coffee shop or restaurant. We were told we could come ..."

Reviewed on 18 May 2026

Oceanfront Private Cottage!

Islamorada FL

Stay at this cottage in Islamorada. Enjoy free Wi-Fi, patios and cable/satellite TV service. Popular attractions History of Diving Museum and Florida Keys Brewing ...

10/10 Exceptional! (117 reviews)

"Host was very responsive when we reached out and the place had everything we needed. The dock for the boat was very easy to get in and out of and we had plenty of room for the trailer. The place was also very clean."

Reviewed on 11 Jun 2026

See all properties in Upper Matecumbe Key

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Upper Matecumbe Key attractions

Bud n' Mary's Dive Center

8.8/5 (504 reviews)

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

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